CA2998681C - Derives d'acide oleanolique modifie en c4 pour l'inhibition de l'il-17 et d'autres utilisations - Google Patents

Derives d'acide oleanolique modifie en c4 pour l'inhibition de l'il-17 et d'autres utilisations Download PDF

Info

Publication number
CA2998681C
CA2998681C CA2998681A CA2998681A CA2998681C CA 2998681 C CA2998681 C CA 2998681C CA 2998681 A CA2998681 A CA 2998681A CA 2998681 A CA2998681 A CA 2998681A CA 2998681 C CA2998681 C CA 2998681C
Authority
CA
Canada
Prior art keywords
substituted
alkyl
hydrogen
alkoxy
compound
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CA2998681A
Other languages
English (en)
Other versions
CA2998681A1 (fr
Inventor
Melean Visnick
Xin Jiang
Martha R. Hotema
Chitase Lee
Bradley William Caprathe
William H. Roark
Gary Bolton
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Reata Pharmaceuticals Inc
Original Assignee
Reata Pharmaceuticals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Reata Pharmaceuticals Inc filed Critical Reata Pharmaceuticals Inc
Publication of CA2998681A1 publication Critical patent/CA2998681A1/fr
Application granted granted Critical
Publication of CA2998681C publication Critical patent/CA2998681C/fr
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J63/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
    • C07J63/008Expansion of ring D by one atom, e.g. D homo steroids
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61PSPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07JSTEROIDS
    • C07J71/00Steroids in which the cyclopenta(a)hydrophenanthrene skeleton is condensed with a heterocyclic ring
    • C07J71/0005Oxygen-containing hetero ring
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02ATECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pain & Pain Management (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Rheumatology (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Steroid Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pyridine Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Thiazole And Isothizaole Compounds (AREA)

Abstract

L'invention concerne des dérivés d'acide oléanolique modifiés en C4 de formule : formule (X) ou formule (XII), ainsi que des analogues de ces derniers, dans lesquelles les variables sont telles que définies dans la description. En outre, l'invention concerne des compositions pharmaceutiques de ces dérivés ou analogues, des procédés pour leur fabrication, et des procédés pour leur utilisation, y compris pour la prévention et le traitement de maladies ou de troubles associés à la surproduction d'IL-17.
CA2998681A 2015-09-23 2016-09-23 Derives d'acide oleanolique modifie en c4 pour l'inhibition de l'il-17 et d'autres utilisations Active CA2998681C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US201562222632P 2015-09-23 2015-09-23
US62/222,632 2015-09-23
PCT/US2016/053545 WO2017053868A1 (fr) 2015-09-23 2016-09-23 Dérivés d'acide oléanolique modifié en c4 pour l'inhibition de l'il-17 et d'autres utilisations

Publications (2)

Publication Number Publication Date
CA2998681A1 CA2998681A1 (fr) 2017-03-30
CA2998681C true CA2998681C (fr) 2024-02-06

Family

ID=57137257

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2998681A Active CA2998681C (fr) 2015-09-23 2016-09-23 Derives d'acide oleanolique modifie en c4 pour l'inhibition de l'il-17 et d'autres utilisations

Country Status (15)

Country Link
US (2) US11584775B2 (fr)
EP (1) EP3353190B1 (fr)
JP (1) JP7074674B2 (fr)
KR (1) KR20180061251A (fr)
CN (1) CN108290922B (fr)
AU (1) AU2016326704B2 (fr)
BR (1) BR112018005861B1 (fr)
CA (1) CA2998681C (fr)
EA (1) EA201890767A1 (fr)
ES (1) ES2865163T3 (fr)
HK (1) HK1258095A1 (fr)
IL (1) IL258185B (fr)
MX (1) MX2018003569A (fr)
NZ (1) NZ741082A (fr)
WO (1) WO2017053868A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2703274T3 (es) 2008-04-18 2019-03-07 Reata Pharmaceuticals Inc Moduladores de la inflamación antioxidantes: derivados del ácido oleanólico con modificaciones amino y otras en C-17
TWI623548B (zh) 2012-04-27 2018-05-11 瑞塔醫藥有限責任公司 齊墩果酸(bardoxolone methyl)之2,2-二氟基丙醯胺衍生物、多晶型及其使用方法
MY180903A (en) 2012-09-10 2020-12-11 Reata Pharmaceuticals Inc C17-alkanediyl and alkenediyl derivatives of oleanolic acid and methods of use thereof
US9512094B2 (en) 2012-09-10 2016-12-06 Reata Pharmaceuticals, Inc. C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
AR096046A1 (es) 2013-04-24 2015-12-02 Abbvie Inc Derivados de 2,2-difluoropropanamida de metil bardoxolona, formas polimórficas y métodos de uso
US10953020B2 (en) 2016-11-08 2021-03-23 Reata Pharmaceuticals, Inc. Methods of treating Alport syndrome using bardoxolone methyl or analogs thereof
CN108299541B (zh) * 2018-01-18 2020-12-11 华南师范大学 海洋微生物来源的二倍半萜AsperterpinolB衍生物及合成方法与抗炎应用
CN108191944B (zh) * 2018-01-18 2020-12-11 华南师范大学 海洋微生物来源的二倍半萜AsperterpinolB衍生物及合成方法与糖酶应用
CN109248168A (zh) * 2018-10-30 2019-01-22 武汉卫无忧生物科技有限公司 齐墩果酸在制备抗幽门螺杆菌的药物中的用途
KR20220044942A (ko) * 2019-07-19 2022-04-12 리아타 파마슈티컬즈, 아이엔씨. C17 극성-치환된 헤테로방향족 합성 트리터페노이드 및 그의 사용 방법
WO2022126129A1 (fr) 2020-12-11 2022-06-16 Reata Pharmaceuticals, Inc. Triterpénoïdes synthétiques destinés à être utilisés en thérapie
AU2022208727A1 (en) * 2021-01-18 2023-08-03 Reata Pharmaceuticals, Inc. Synthetic ursolic acid derivatives and methods of use thereof
CN113185570A (zh) * 2021-05-12 2021-07-30 张洪胜 一种治疗银屑病的齐墩果酸衍生物及其制备方法

Family Cites Families (65)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4395423A (en) 1978-10-10 1983-07-26 Sterling Drug Inc. Polycyclic cyanoketones
US5064823A (en) 1988-08-24 1991-11-12 Research Triangle Institute Pentacyclic triterpenoid compounds as topoisomerase inhibitors or cell differentiation inducers
DE19817262A1 (de) 1998-04-18 1999-10-21 Bayer Ag Neue 2-heterocyclisch substituierte Dihydropyrimidine
US6326507B1 (en) 1998-06-19 2001-12-04 Trustees Of Dartmouth College Therapeutic compounds and methods of use
US6369101B1 (en) 1999-02-26 2002-04-09 Regents Of The University Of Minnesota Therapeutic method to treat herpes virus infection
BR0011522A (pt) 1999-05-14 2002-06-04 Nereus Pharmaceuticals Inc Composto e método de sintetização para a fabricação do composto
US6649654B1 (en) 1999-11-23 2003-11-18 The Regents Of The University Of California Methods for identifying and using IKK inhibitors
WO2002003996A1 (fr) 2000-07-12 2002-01-17 RAJKUMAR, Sujatha Utilisation de saponines de triterpenoide de type dammarane
US6951847B2 (en) 2000-09-29 2005-10-04 Regents Of The University Of Minnesota Methods of treating fungal infections using lupeol
AU2001294959A1 (en) 2000-09-29 2002-04-08 Robert M. Carlson Triterpenes having antibacterial activity
US6642217B2 (en) 2000-09-29 2003-11-04 Naturtek, Llc Triterpenes having human antifungal and antiyeast activity
US6878751B1 (en) 2000-10-19 2005-04-12 Imperial College Of Science Technology And Medicine Administration of resveratrol to treat inflammatory respiratory disorders
US7435755B2 (en) 2000-11-28 2008-10-14 The Trustees Of Dartmouth College CDDO-compounds and combination therapies thereof
CA2430454A1 (fr) 2000-11-28 2002-06-20 Board Of Regents, The University Of Texas System Composes cddo et polytherapies associees
WO2002092768A2 (fr) 2001-05-14 2002-11-21 University Of Maryland, Baltimore Nouvelle enzyme transaminase alanine et procedes d'utilisation de celle-ci
US7176237B2 (en) 2002-01-15 2007-02-13 The Trustees Of Dartmouth College Tricyclic-bis-enone derivatives and methods of use thereof
DE60325329D1 (de) 2002-01-18 2009-01-29 Univ Minnesota Quaternäre terpensalze als biologisch aktive tenside
EP1507541A4 (fr) 2002-05-13 2009-06-03 Dartmouth College Inhibiteurs et procedes d'utilisation de ceux-ci
US20050014730A1 (en) 2003-04-02 2005-01-20 Carlson Robert M. Anti-fungal formulation of triterpene and essential oil
AU2005282437B2 (en) 2004-09-07 2013-01-10 Pacific Arrow Limited Anti-tumor compounds with angeloyl groups
WO2005042002A2 (fr) 2003-10-30 2005-05-12 Entelos, Inc. Traitement de la polyarthrite rhumatoide a l'aide d'antagonistes de la proteine flip
WO2005046732A2 (fr) 2003-11-04 2005-05-26 THE UNITED SATES OF AMERICA as represented by THE SECRETARY OF HEALTH AND HUMAN SERVICES, NIH Methodes et compositions d'inhibition de la replication du vih-1
US20060258752A1 (en) 2004-02-12 2006-11-16 Vander Jagt David L Method and compounds for cancer treatment utilizing NFkB as a direct or ultimate target for small molecule inhibitors
JP2005314381A (ja) 2004-03-30 2005-11-10 Anges Mg Inc 増殖性腎疾患の予防・治療・改善剤
EP1959969A2 (fr) 2005-07-01 2008-08-27 The Johns Hopkins University Compositions et procedes pour traiter ou prevenir des troubles associes au stress oxydatif
EP1996205A2 (fr) 2006-03-23 2008-12-03 Advanced Life Sciences Inc. Triterpenoides pentacycliques synthetiques et derives d'acide betulinique et de betuline
US20070249561A1 (en) 2006-04-25 2007-10-25 Taylor Bradley K Pharmacological method for treatment of neuropathic pain
WO2008000068A1 (fr) 2006-06-27 2008-01-03 Wellington Laboratories Inc. Procédé de préparation de composés 2-iodo triterpénoïdes
WO2008016095A1 (fr) 2006-08-02 2008-02-07 Santen Pharmaceutical Co., Ltd. REMÈDE PRÉVENTIF OU CURATIF POUR LES KÉRATOCONJONCTIVITES CONTENANT UN ACTIVATEUR DE Nrf2 EN TANT QUE MATIÈRE ACTIVE
US8299046B2 (en) 2006-11-17 2012-10-30 Trustees Of Dartmouth College Synthetic triterpenoids and tricyclic-bis-enones for use in stimulating bone and cartilage growth
WO2008064133A1 (fr) 2006-11-17 2008-05-29 Trustees Of Dartmouth College Synthèse et activités biologiques de nouveaux composés tricycliques-bis-énones (tbe)
LT2653873T (lt) 2007-02-08 2022-10-10 Biogen Ma Inc. Kompozicijos ir naudojimas, skirti išsėtinei sklerozei gydyti
WO2008111497A1 (fr) 2007-03-08 2008-09-18 Santen Pharmaceutical Co., Ltd. Agent prophylactique ou thérapeutique pour une maladie ophtalmique associée avec un stress oxydant, comprenant un triterpénoïde comme principe actif
WO2008136838A1 (fr) 2007-05-04 2008-11-13 Trustees Of Dartmouth College Nouveaux dérivés d'amide de cddo et leurs procédés d'utilisation
US20090048205A1 (en) 2007-08-15 2009-02-19 Colin Meyer Combination therapy with synthetic triterpenoids and gemcitabine
US8088824B2 (en) 2007-08-15 2012-01-03 Reata Pharmaceuticals Inc. Forms of CDDO methyl ester
WO2009058849A1 (fr) 2007-10-29 2009-05-07 University Of Rochester Utilisation de composés électrophiles pour induire une production plaquettaire ou maintenir une fonction plaquettaire
JP4923146B2 (ja) 2008-01-11 2012-04-25 リアタ ファーマシューティカルズ インコーポレイテッド 合成トリテルペノイドおよび疾患の治療における使用方法
ES2703274T3 (es) 2008-04-18 2019-03-07 Reata Pharmaceuticals Inc Moduladores de la inflamación antioxidantes: derivados del ácido oleanólico con modificaciones amino y otras en C-17
JP5564490B2 (ja) 2008-04-18 2014-07-30 リアタ ファーマシューティカルズ インコーポレイテッド 抗炎症性ファルマコアを含む化合物および使用法
CN102164941B (zh) 2008-04-18 2015-05-27 里亚塔医药公司 抗氧化剂炎症调节剂:具有饱和c环的齐墩果酸衍生物
WO2009146216A2 (fr) 2008-04-18 2009-12-03 Reata Pharmaceuticals. Inc. Modulateurs d’inflammation antioxydant : nouveaux dérivés d’acide oléanolique
EP2271658B1 (fr) 2008-04-18 2016-11-09 Reata Pharmaceuticals, Inc. Modulateurs d'inflammation antioxydants : dérivés d'acide oléanolique c-17 homologués
CN101298466B (zh) 2008-06-13 2014-04-09 南京大学 齐墩果酸衍生物及其制备方法和应用
US8314137B2 (en) 2008-07-22 2012-11-20 Trustess Of Dartmouth College Monocyclic cyanoenones and methods of use thereof
WO2010053817A1 (fr) 2008-11-04 2010-05-14 Trustees Of Dartmouth College Dérivés de l’acide bétulinique et leurs méthodes d’utilisation
SI2395979T1 (sl) 2009-02-13 2017-12-29 Reata Pharmaceuticals, Inc. Peroralni farmacevtski sestavki, ki vsebujejo amorfni CDDO-Me, z zapoznelim sproščanjem
WO2011130302A2 (fr) 2010-04-12 2011-10-20 Reata Pharmaceuticals, Inc. Procédés de traitement de l'obésité utilisant des modulateurs d'inflammation antioxydants
US8618125B2 (en) * 2011-01-14 2013-12-31 Heptiva LLC Composition comprising hepatic therapeutic active for treating liver diseases, certain cancers and liver health maintenance
CA2826113C (fr) 2011-01-31 2018-09-04 Bristol-Myers Squibb Company Triterpenoides modifies en c-17 et c-3 presentant une activite inhibitrice de la maturation du vih
ME03469B (fr) 2011-03-11 2020-01-20 Reata Pharmaceuticals Inc Dérivés monométhyle triterpénoïdes en c4 et leurs procédés d'utilisation
US8987502B2 (en) 2011-12-01 2015-03-24 Hangzhou Bensheng Pharmaceutical Co., Ltd. Oleanolic acid amidate derivatives, preparation methods and uses thereof
TWI623548B (zh) 2012-04-27 2018-05-11 瑞塔醫藥有限責任公司 齊墩果酸(bardoxolone methyl)之2,2-二氟基丙醯胺衍生物、多晶型及其使用方法
US8921419B2 (en) 2012-05-08 2014-12-30 Trustees Of Dartmouth College Triterpenoids and compositions containing the same
WO2013169740A2 (fr) 2012-05-08 2013-11-14 Trustees Of Dartmouth College Triterpénoïdes synthétiques et procédés pour moduler l'expression de gènes de cellules souches/progénitrices
US9556222B2 (en) 2012-06-15 2017-01-31 Reata Pharmaceuticals, Inc. A-ring epoxidized triterpenoid-based anti-inflammation modulators and methods of use thereof
CN103665087A (zh) * 2012-09-03 2014-03-26 上海源力生物技术有限公司 一种萜类化合物及其在医药上的应用
DK2892911T3 (en) 2012-09-10 2017-10-23 Reata Pharmaceuticals Inc C17 heteroaryl derivatives of oleanolic acid and methods of use thereof
US9278912B2 (en) 2012-09-10 2016-03-08 Reata Pharmaceuticals, Inc. C13-hydroxy derivatives of oleanolic acid and methods of use thereof
US9512094B2 (en) 2012-09-10 2016-12-06 Reata Pharmaceuticals, Inc. C17-heteroaryl derivatives of oleanolic acid and methods of use thereof
MY180903A (en) 2012-09-10 2020-12-11 Reata Pharmaceuticals Inc C17-alkanediyl and alkenediyl derivatives of oleanolic acid and methods of use thereof
TWI716341B (zh) 2013-08-23 2021-01-21 美商瑞塔醫藥有限責任公司 使用齊墩果酸(bardoxolone methyl)或其類似物治療和預防內皮功能障礙之方法
CN104861027A (zh) 2014-02-24 2015-08-26 上海兰蒂斯生物医药科技有限公司 新型齐墩果酸衍生物、其制备方法及其应用
US9896475B2 (en) 2014-08-26 2018-02-20 Trustees Of Dartmouth College Pyridyl analogs of 1-(2-cyano-3,12-dioxooleana-1,9(11)dien-28-oyl) imidazole
US10953020B2 (en) 2016-11-08 2021-03-23 Reata Pharmaceuticals, Inc. Methods of treating Alport syndrome using bardoxolone methyl or analogs thereof

Also Published As

Publication number Publication date
NZ741082A (en) 2023-06-30
EA201890767A1 (ru) 2019-09-30
EP3353190A1 (fr) 2018-08-01
KR20180061251A (ko) 2018-06-07
AU2016326704B2 (en) 2021-01-28
AU2016326704A1 (en) 2018-04-26
WO2017053868A1 (fr) 2017-03-30
CN108290922A (zh) 2018-07-17
ES2865163T3 (es) 2021-10-15
US20190153022A1 (en) 2019-05-23
US11584775B2 (en) 2023-02-21
JP7074674B2 (ja) 2022-05-24
IL258185A (en) 2018-05-31
CA2998681A1 (fr) 2017-03-30
MX2018003569A (es) 2018-11-29
BR112018005861A2 (pt) 2018-10-16
US20230250130A1 (en) 2023-08-10
WO2017053868A8 (fr) 2018-04-19
IL258185B (en) 2021-08-31
CN108290922B (zh) 2021-12-07
HK1258095A1 (zh) 2019-11-01
EP3353190B1 (fr) 2021-03-17
BR112018005861B1 (pt) 2022-11-22
JP2018528275A (ja) 2018-09-27

Similar Documents

Publication Publication Date Title
CA2998681C (fr) Derives d'acide oleanolique modifie en c4 pour l'inhibition de l'il-17 et d'autres utilisations
CA2829618C (fr) Derives monomethyle triterpenoides en c4 et leurs procedes d'utilisation
DK2892911T3 (en) C17 heteroaryl derivatives of oleanolic acid and methods of use thereof
US9278912B2 (en) C13-hydroxy derivatives of oleanolic acid and methods of use thereof
MX2010011437A (es) Moduladores antioxidantes de inflamacion: derivados del acido oleanolico con saturacion en el anillo c.
BR112013015241A2 (pt) enonas tricíclicas de pirazolila e pirimidinila como moduladores de inflamação antioxidantes
CA2974726C (fr) Enones tricycliques d'imidazolyle comme modulateurs antioxydants de l'inflammation
WO2021127480A1 (fr) Triterpénoïdes synthétiques comprenant des substituants à base d'azote en c-17 et leurs méthodes d'utilisation
EA041119B1 (ru) C4-модифицированные производные олеаноловой кислоты для ингибирования il-17 и содержащие их фармацевтические композиции
TW202245795A (zh) 合成之熊果酸衍生物及其使用方法
CA3144603A1 (fr) Triterpenoides synthetiques heteroaromatiques a substitution polaire c17 et leurs procedes d'utilisation

Legal Events

Date Code Title Description
EEER Examination request

Effective date: 20210920

EEER Examination request

Effective date: 20210920

EEER Examination request

Effective date: 20210920

EEER Examination request

Effective date: 20210920

EEER Examination request

Effective date: 20210920

EEER Examination request

Effective date: 20210920

EEER Examination request

Effective date: 20210920

EEER Examination request

Effective date: 20210920